4

それだって、実際に選んでみないことにはわからないのだ。

I often see something like 私にわからない meaning "I don't understand", but what does it mean when the particle に attaches to こと?

From the context I think what this sentences means is "Nevertheless, I must try to make a choice". So I'm thinking ことにはわからない means something like "it is not possible" but I don't see that supported in any of the dictionaries where I checked the definitions of わかる.

5

(A) + ないことには + (B) + ない is a fixed construction meaning "not (B) if not (A)" or "not (B) without/unless (A)".

実際に選んでみないことにはわからないのだ。
I don't understand it unless I actually choose it.

JGram has many examples of this pattern. (Note: This page contains some examples not related to this pattern. Ignore examples #259 and #5258 for now.)

This ~ないことには is interchangeable with ~ないと/~なければ, but it sounds slightly stiffer, I think. And ~ないことには is almost always followed by another negative expression.

  • 宿題をしないと怒られる。: OK
  • 宿題をしなければ怒られる。: OK
  • 宿題をしないことには怒られる。: awkward
  • 宿題をしないことには眠れない。: OK

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